Pretty Tough with Maria Sharapova

Ariel Investments Co-CEO and former Starbucks Chair Mellody Hobson joins Maria Sharapova on Pretty Tough to share the lessons behind her successful career in business and investing. From joining Ariel as a college student to becoming co-CEO more than three decades later, Mellody opens up about the power of long-term commitment, leading with confidence, and what it takes to succeed in rooms where you’re underestimated.

Mellody shares how she built a successful co-CEO partnership with Ariel founder John Rogers, the importance of self-awareness in leadership, and why preparation has been key to her success. She also reflects on how growing up with financial insecurity inspired her passion for financial literacy, the money lessons she’s passing on to her daughter, and why she believes women’s sports are one of the biggest investment opportunities of our time.

00:00 — Introduction: Meet Mellody Hobson, Co-CEO of Ariel Investments and Boardroom Trailblazer

01:15 — The Art of War in Business: Why Sometimes You Have to "Crouch to Conquer"

04:30 — Building a 30-Year Career at a Single Firm: Knowing When to Stay vs. When to Leave

07:45 — David Geffen’s Brutal Advice: The 40-Year-Old Moment of Truth and Recommitment

12:00 — Leadership Lessons: Owning Your Mistakes and Choosing Intellectual Honesty Over Excuses

15:00 — Surviving Underestimation: Why Preparation and Deep Knowledge Beat Low Expectations Every Time

17:30 — Negotiating Co-CEO Life: Setting Rules of Engagement and Treating Your Co-Founder Like a Board Member

24:00 — "Life Is Don't Make It Harder": Managing Crisis, Financial Meltdowns, and Unpredictable Eras

27:30 — From Childhood Evictions to Financial Mastery: Turning Trauma Into Purpose

33:00 — Managing Abundance: Overcoming the Underlying Anxiety of Growing Up with Insecurity

35:00 — Demystifying Money on Good Morning America: The Power of Clear Language and No Acronyms

38:00 — Breaking the Money Taboo: Why Parents Struggle to Talk Credit Cards and Financial Habits with Kids

44:00 — Sports Obsession and the Massive Economic Wave of Women’s Sports Investments

48:45 — Inside the Lucas Museum of Narrative Art: George Lucas’s 17-Year Vision and the $2 Grilled Cheese

54:30 — Co-Leadership in Marriage: The Power of Genuine Respect, Loyalty, and Not Being Hysterical at the Same Time

58:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Aggression, Jump Rope Milestones, and Finding Strength in the Gym

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LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254CHAPTERS[INSERT

FOLLOW THE SHOW

►Maria on Instagram: https://www.instagram.com/mariasharapova/

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About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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Renowned psychotherapist and relationship expert Esther Perel joins Maria Sharapova on Pretty Tough to explore why modern dating feels so exhausting and what makes long-term relationships lose their spark. Esther explains why dating has become more like a job interview, how the qualities we initially love about our partners can become sources of conflict, and what couples can do to break out of the same arguments.

She also shares her experience conducting couples therapy between a man and his AI girlfriend, raising questions about intimacy, infidelity, and the future of human connection. Plus, Esther shares why being the first to apologize can change the course of an argument.

SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1

LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

CHAPTERS00:00 — Introduction: Meet Esther Perel and the Evolution of Relationship Psychology

01:45 — Surviving vs. Living: The Existential Difference Between Being Alive and Fully Engaged

04:30 — The Power of Mentorship: How Esther Built Her Career Through Curiosity and Boldness

05:45 — From Clinician to Global Public Health Campaign: Why Relationships Need "Practice"

09:45 — The Art of Reflective Listening: Why Most People Only Listen for 10 Seconds

13:00 — Playing the Workplace Card Game: Esther’s Biggest Feedback Lesson

16:30 — Taking Therapy to the Big Screen: Inside the Movie The Invite and Penelope Cruz's Character

22:00 — Mating in Captivity: Reconciling the Eternal Paradox of Safety and Adventure

31:15 — Modern Dating Fatigue: Why the "Checklist" Approach Destroys Romance

40:00 — The First Human-AI Couples Therapy Session: Is Loving a Chatbot an Affair?

47:30 — Who Holds the Power? Why the Person Who Apologizes First Interrupts the Pattern

52:15 — Refusing to Choose: How Ambitious Women Can Hold Both Ambition and Vulnerability Without Burning Out

56:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Rumination and Embracing Directness

FOLLOW THE SHOW►Maria on Instagram: https://www.instagram.com/mariasharapova/►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en

About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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Film Exec Donna Langley joins Maria Sharapova on Pretty Tough to discuss what it's like making consequential decisions at a critical time for the industry.

Donna shares stories about bringing Christopher Nolan to Universal, acquiring the hit horror film Obsession sight unseen, and having the courage to back Wicked after a failed musical. She also talks about finding her own leadership style in a male-dominated industry, without giving up compassion or competitiveness.

SUBSCRIBE
►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1
LISTEN:
►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

CHAPTERS
00:00 — Introduction: Meet Donna Langley, the First British Woman to Run a Major Hollywood Studio
02:00 — Leadership by Doing: Why Decency Is a Superpower, Not a Weakness
05:15 — The "Velvet Hammer": Navigating a Male-Dominated Industry Without Losing Your Grace
07:30 — The $150M Gamble: Landing Christopher Nolan and Winning Big with Oppenheimer
14:30 — The Art of Tough Feedback: How to Deliver Hard News with Empathy
17:15 — Spotting "White Space": Trusting Your Gut and Finding Cultural Blind Spots
19:45 — Dusting Yourself Off: Owning Your Mistakes and Overcoming Creative Failure
25:00 — Inside Christopher Nolan's Library: The Intimidating Tradition of Reading a Script Blind
27:15 — Decisive Leadership: Bidding Wars, Overpaying for Obsession, and Managing Risk
32:00 — Accountability as Freedom: How Sitting in Discomfort Makes You a Better Leader
35:45 — The Shared Human Experience: Why the Magic of Movie Theaters Can't Be Replaced
40:00 — The Future of Cinema: AI, Industry Consolidation, and Protecting the Creative Workforce
43:00 — Falling Forward: From an LA Nightclub VIP Room to the Top of Hollywood
46:15 — Championing Get Out: Why Supporting Unconventional Visionaries Pays Off
48:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Imposter Syndrome and the Myth of Perfection

FOLLOW THE SHOW
►Maria on Instagram: https://www.instagram.com/mariasharapova/
►Maria on X: https://x.com/MariaSharapova
►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en

About Pretty Tough
Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.

Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova
Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.
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Are you feeling stuck? Maria Sharapova sits down with New York Times bestselling author, entrepreneur, and life coach Marie Forleo to discuss building a successful life and career on your own terms. Together they unpack what it takes to overcome self-doubt and how to navigate life's biggest transitions.

Maria and Marie explore the importance of trusting your intuition, managing distractions, and finding the courage to reinvent yourself at any stage of life. Marie also opens up about her nontraditional path to success and how personal challenges led to her taking a five-month sabbatical after 25 years in business.

SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1

LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

CHAPTERS:

00:00 — Introduction: Meet Marie Forleo

01:25 — "Clarity Comes from Engagement, Not Thought": The 10-Year Test

04:15 — Taking the First Step: Joining Broadway Dance Center in Her 20s

06:05 — Fear of Failure vs. Fear of Success: Overcoming Mindset Blocks

08:15 — Feedback as Freedom

09:30 — Starting Out at 23: From Wall Street to Life Coaching

11:45 — The Fork in the Road: Choosing Life Coaching Over Vogue

15:45 — Flipping the Script: Replacing Negative Self-Talk

19:25 — "I Can't" vs. "I Won't": Getting Honest with Yourself

22:00 — Hustling with Integrity: Side Gigs and Financial Independence

24:30 — Understanding Your Risk DNA: All-In vs. Day-Job Entrepreneurs

27:30 — Bootstrapping, Freedom, and Defining Success on Your Own Terms

29:45 — Finding the Right Support: When and How to Hire Help

31:40 — Red Flags to Watch Out for When Choosing a Coach

33:30 — Cutting Through the Noise: Stillness Practices and Social Media Limits

39:15 — Multi-Passionate Focus: Managing Seasons of Exploration vs. Execution

42:45 — Marie's 5-Month Sabbatical: Depletion, Healing, and Listening to Your Soul

46:30 — Pretty Tough Questions: Unlearning Growth at All Costs

FOLLOW THE SHOW

►Maria on Instagram: https://www.instagram.com/mariasharapova/

►Maria on X: https://x.com/MariaSharapova

►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en

About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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Maria Sharapova sits down with celebrity designer Vera Wang. Before becoming one of the most recognized names in fashion, Vera trained as a competitive figure skater with dreams of making the Olympic team. When that dream fell short, she pivoted to fashion.

Vera opens up about her years at Vogue and Ralph Lauren, and the search for her own wedding dress that inspired her bridal business at 40, selling the company she spent decades building and her mindset around reinventing yourself.

SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1

LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

CHAPTERS

00:00 — Introduction: Meet Vera Wang and Her Legendary Career

02:00 — Figure Skating as a Metaphor for Life and Learning How to Fall

05:30 — The 1968 Olympic Trials Heartbreak and Pivoting After Skating

10:30 — Moving to Paris, Discovering Fashion, and Starting at Vogue

14:45 — Mentorship, Ralph Lauren, and Working Alongside Anna Wintour

18:45 — Turning 40, Searching for a Wedding Dress, and Launching a Bridal Empire

24:30 — The Difference Between Male and Female Designers and Feeling the Clothes

27:15 — Running a Business for 35 Years: The Sweat, Recessions, and Hard Decisions

36:15 — Age Defying, Personal Style, and Feeling Truthful to Yourself

41:30 — Looking at Young Designers, Mentorship, and the Role of AI in Fashion

48:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Perfection

FOLLOW THE SHOW

►Maria on Instagram: https://www.instagram.com/mariasharapova/

►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en

About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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